Novel Chiral Helical Polyisocyanides Containing Cyclohexanediamine Pendants for Asymmetric Michael Addition Reaction and Aldol Reaction

A novel helical poly(phenylisocyanide)-supported catalyst bearing (1 R ,2 R )-1,2-cyclohexanediamine pendant (poly-2 m ) was synthesized. The chiral cyclohexanediamine polymer catalyst exhibited superior catalytic activity and stereoselectivity in the Michael addition reaction. The polymer poly-2 200 catalyzed the Michael addition reaction of cyclohexanone with trans-nitrosostyrene in methanol at the presence of benzoic acid with an enantiomeric excess ( ee ) value up to 97% and diastereoselectivity ( dr ) value of 79/21. In addition, the chiral polymer catalyst can be recycled for 3 times in the asymmetric Michael addition reaction without significantly lossing the catalytic activity of the catalyst. Moreover, the chiral cyclohexanediamine catalyst poly-2 200 can also catalyze the Aldol reaction of p -nitrobenzaldehyde with cyclohexanone, with ee value of 49% and dr value of 60/40. Graphical Abstract Asymmetric Michael addition reaction and Aldol reaction catalyzed by poly-2 m